374681-00-2Relevant articles and documents
A convergent synthesis of the 11-oxa prostaglandin analogue AL-12182
Fox, Martin E.,Jackson, Mark,Lennon, Ian C.,McCague, Raymond
, p. 1227 - 1236 (2005)
(Chemical Equation Presented) The 11-oxa prostaglandin analogue AL-12182 1 has potent topical ocular hypotensive activity. A convergent and concise general synthesis of this class of prostanoid was developed employing a stereoselective coupling reaction between a tetrahydrofuran core electrophile and a nucleophilic omega side chain component, providing a route that should be suitable for commercial scale production. The tetrahydrofuran core was assembled from dimethyl D-malate using a stereoselective β-hydroxy ester dianion alkylation reaction.
Phainanoids A-F, A new class of potent immunosuppressive triterpenoids with an unprecedented carbon skeleton from phyllanthus hainanensis
Fan, Yao-Yue,Zhang, Hua,Zhou, Yu,Liu, Hong-Bing,Tang, Wei,Zhou, Bin,Zuo, Jian-Ping,Yue, Jian-Min
, p. 138 - 141 (2015/01/30)
Phainanoids A-F (1-6), six highly modified triterpenoids with a new carbon skeleton by incorporating two unique motifs of a 4,5- and a 5,5-spirocyclic systems, were isolated from Phyllanthus hainanensis. Their structures with absolute configurations were determined by spectroscopic data, chemical methods, and X-ray crystallography. Compounds 1-6 exhibited exceptionally potent immunosuppressive activities in vitro against the proliferation of T and B lymphocytes. The most potent one, phainanoid F (6), showed activities against the proliferation of T cells with IC50 value of 2.04 ± 0.01 nM (positive control CsA = 14.21 ± 0.01 nM) and B cells with IC50 value of 1.60 ± 0.01 nM (CsA = 352.87 ± 0.01 nM), which is about 7 and 221 times as active as CsA, respectively. The structure-activity relationships of 1-6 are discussed.
Synthesis of the C-18-C-34 fragment of amphidinolides C, C2, and C3
Clark, J. Stephen,Yang, Guang,Osnowski, Andrew P.
, p. 1464 - 1467 (2013/06/27)
The C-18-C-34 fragment of amphidinolides C, C2, and C3 and the C-18-C-29 fragment of amphidinolide F have been constructed from a trans-2,5-disubstituted dihydrofuran. This key intermediate was prepared from a dihydrofuranone formed by diastereoselective rearrangement of a free or metal-bound oxonium ylide generated from a metal carbenoid. The side chains found in amphidinolides C and F were introduced using Sonogashira coupling reactions.
